I agree about RI and MA. CT isn't beachy that way. When I lived in CT we'd go to RI a lot.

Litchfield County is another option, and very pretty, though I got Lyme disease after spending a week there.

A bit off topic but I associate them both with year-round living for downwardly mobile old money families from slightly farther north

I live in CT too but it is not great for beaches being on that side of the Long Island Sound.

For New England beaches, I much prefer Watch Hill and Newport in RI; Cape Cod, Nantucket and Martha's Vineyard in MA.

RI is only a little bit farther and the beaches are VASTLY superior. Nicer than Cape Cod too IMO.

To me they are “on the water” but not “beach towns.”

I know people who live there year-round, so to me it’s not as “beachy” as Delaware (though maybe there are other areas that are more vacation house dominated. The people I know in that area are wealthy retired people, and that’s their main house.

I did not find Old Saybrook as charming as I expected to. It’s not much like the DE beaches at all.

Don’t bother, the LI sound beaches aren’t worth it. Either keep driving to RI or, if CT really makes the most sense logistically, stay someplace inland like Litchfield which has great restaurants, hiking, biking, and kayaking.

I’m from CT, live in dc area now but my family is all up there so we try to find places near them because I can drive more.

I can tell you right now there are no CT beach towns or even towns that I would spend more than 2-3 days in and I love CT.

Where I would go instead:

Cape Cod
Newport/Narragansett RI
Finger Lakes or Lake George in NY
The Hamptons
NYC, Philly or Boston
Northern NJ beach towns like OCNJ, point Pleasant and LBI

Here’s some more CT info: https://www.dcurbanmom.com/jforum/posts/list/974360.page

Lyme has Lyme. Be careful.

I don’t know the area well but I do know that Fenwick and Old Black Point are where old money families go and tend to spend the summer. Lyme has a lot of NYC country home owners and a lot of retirees.
Lots of stuff to do - go to Mystic and Stonington and Watch Hill RI for day trips.

Mostly families renting a week or own their own house. They tend to cook at home and go out once or twice.

Logistically, this seems a good "middle" to meet up with family/friends for a summer holiday, but I'm not very familiar with CT beach towns. What types of people vacation there? Is it mainly older retirees (that's what I'm seeing in restaurant photos)?
Are there many families that own homes/spend their summers in these towns?
Or is it more likely weekly rentals?
Is this area bikeable? Do people go back and forth between the 2 towns, Old Saybrook and Old Lyme for dinner, etc, or do you pick one and sort of stay there?
Is there much to do for teens?

Also, could anyone give me a breakdown of each CT beach towns' individual vibe, and how they would match up to say, Delaware beach towns, as a reference point?